Phenol on treatment with CO2 in the presence of NaOH followed by acidification produces compound X as the major product. X on treatment with (CH3CO)2O in the presence of catalytic amount of H2SO4 produces :
(A)(see structure)
(B)(see structure)✓ Correct
(C)(see structure)
(D)(see structure)
Answer: (B)
Solution
Phenol with COX2 and NaOH followed by acidification is the Kolbe-Schmitt route to salicylic acid, so X is 2-hydroxybenzoic acid. Treating that phenolic −OH with acetic anhydride under a trace of acid acetylates it, and the product is acetylsalicylic acid, that is aspirin.
JEE Main · 2018 · 08 Apr 2018 · Offline · Single correct option